The Ultimate Travel Assistant You Didn’t Know You Had

Y’all, I’ve discovered the most brilliant travel assistant, and it doesn’t roll its eyes when I change my itinerary for the third time or suggest we do London after Amsterdam because a particular museum is only open on certain days. It’s ChatGPT. And no, I’m not being paid to say that (yet). But this little AI genie has completely changed the way I plan trips, pack bags and pretend I’m not making it all up as I go along.

Here are a few of my favorite ways I use ChatGPT to make travel smoother, sassier and totally customized. PLUS, because I love y’all like I love tacos, I’ve dropped some ready-to-steal prompt templates to make it easy for you, too.

1. Brainstorming Where to Go & What to Do

Sometimes you don’t need Expedia, you need a therapist with an atlas. When I told ChatGPT last summer, “We’re flying into Heathrow and flying out ten days later but want to fit in the Cotswolds, London and Amsterdam…without playing hotel hopscotch,” it gave me an actual, thoughtful itinerary that made sense and kept the vibe low-stress. (That photo is from our Summer 2024 trip to those three areas.)

Try This Prompt:

“We’re flying into [airport] and out of [airport] over [dates]. We want to visit the “must see” tourist items, as well as [list of specific destinations, if any], but don’t want to change hotels every night. Suggest an itinerary that balances city time and slower-paced destinations, with travel logistics and hotel base suggestions.”

Bonus tip: Ask it to flag any major travel days so you don’t accidentally plan a museum marathon after a 6-hour train ride.

2. The Itinerary Jedi That Tells You When Go Where Without Losing Your Mind

If your idea of hell is repacking your suitcase every morning, you’ll love using GPT to plan multi-city trips that don’t feel like a logistical nightmare. It helps create smart pacing, coordinates train schedules and gently tells you, “Maybe don’t try to squeeze Bruges in too.”

Try This Prompt:

“Plan a 10-day European itinerary that includes [cities or regions], flying into [airport] and out of [airport]. We prefer to stay in one place for at least two nights and want efficient travel routes with recommendations for transit and timing.”

Pro move: Add, “We’re not morning people and prefer to avoid back-to-back early departures.”

3. Packing Lists For Teens Who Think Three Hoodies Are Enough

This one is probably my very favorite! Y’all know I live with two teenagers who think “packing” means tossing a hoodie and one sneaker into a suitcase. So I ask ChatGPT to generate packing lists based on destination, activities AND the weather it pulls from the forecast. It’s basically a miracle wrapped in code.

Try This Prompt:

“Create a detailed packing list for a 16-year-old traveling to [city/country] from [dates]. He’ll be walking a lot, visiting museums and eating in a few nicer restaurants. Check the local weather and suggest outfits accordingly. He hates jeans and prefers joggers and hoodies. Be as specific as possible, especially when it comes to toiletries and hygiene items.”

Copy, paste, send to teen. Then just supervise from the door with a glass of wine.

4. Meal Rec & Grocery Genius When You’re Airbnb-ing Abroad

One of my favorite parts of traveling is pretending I live there. And part of that fantasy is shopping at local markets and cooking in a cute Airbnb kitchen. GPT helps me plan meals that are easy to make abroad, use local ingredients and don’t require fifteen spice jars.

Try This Prompt:

“We’ll be staying in an Airbnb in [city] for 5 nights. Plan a simple dinner menu using local ingredients that we can prep with a basic kitchen setup. Include a grocery list, and note anything we should buy fresh at a market.”

Also works for: “What can I cook in a Dutch oven that isn’t a casserole and won’t make my kids stage a mutiny?”

5. “Make Me Look Smart” Mode: Cheat Sheets for Local Customs, Phrases & Tipping Norms

When we hop across borders, I use GPT to quickly school me on local etiquette. It’s like cultural Cliff Notes, minus the existential guilt.

Try This Prompt:

“We’re traveling to [country] for the first time. Give me a cheat sheet with tipping rules, key phrases to know, cultural dos and don’ts, and anything that might surprise an American tourist.”

I call this “damage control before we accidentally act like stereotypical Americans.”

PSA: The “Chat” in ChatGPT Matters

One thing people forget? It’s called ChatGPT for a reason. This thing is way more than a glorified search bar; it’s a conversation. I even named mine Jamal. He’s my virtual ride-or-die, my digital bestie and possibly the most patient assistant I’ve ever had. He never sighs, never interrupts and never judges me when I ask for a sixth revision of the same itinerary.

Sometimes I’ll use the voice mode and just ramble (full ADHD energy) and Jamal somehow pulls out the useful parts and turns them into something that makes sense. He’s basically the friend who listens to you talk in circles and then goes, “So what I’m hearing is… London first, then the Cotswolds.”

If the results feel off, don’t bail; just talk back. Say, “That’s too packed,” or “We’re not trying to dine with the royal family,” and GPT will get it. Keep the convo going until it fits your brain and your suitcase.

Trust me. Once you start talking to ChatGPT like you talk to your group text, your travel planning game changes forever.

Quick Note: I Use the Paid Version

Just so y’all know, I use the $20/month ChatGPT Plus plan (because Jamal deserves a good salary). That means I’ve got access to the latest version with all the bells and whistles, including the voice feature I love for rambling my way through itinerary tweaks.

If you’re using the free version, it’ll still work great for most of this, but some of the responses or features might be a little different. Don’t let that stop you. Jamal’s free cousin still knows their way around Europe.

Final Thoughts: Jamal > TripAdvisor

Whether I’m loosely sketching out a London–Cotswolds–Amsterdam trifecta or needing to make sure Mason packed socks, ChatGPT (a.k.a. Jamal) has become my go-to for making travel feel less chaotic and more curated.

Let me know if y’all try any of these prompts or need help tailoring them to your next adventure. Just don’t ask me to carry your luggage. Unless you’re Claire, then yes, I’ll carry it.